Yeah, it depends. (And notice that I prefaced that quote with "
unless their measurements are perfect on both the pole AND the hole in the ground..." I didn't say they can't do it, I said they can't unless they go through some slightly extra work.)
Digging a hole to a strict, precise depth takes longer and is more tedious, time consuming work than just lopping the top off afterwards. Sometimes it's easier to dig to "at least" a certain depth, drop in the pole, then chop the top. I know they do this in fence building so often because there are dozens of fence post holes to dig and it's easier to make sure the tops are beautifully aligned. It's nearly impossible to measure the depth of a hole precisely without making the bottom perfectly flat and even - again, something that is hard to do... they often dig through the dirt then toss in granular stones to pad the bottom, in which case it takes a lot of trial and error measuring in order to get it perfect. But I'm going mostly on knowledge of fence post installation rather than large pole installation.
It basically ends up being more tedious to make a precise hole than to just dig "deep enough" and saw off the top when you're done. But it definitely depends on the job and I will admit I'm not a pole installer.

The telephone poles in Cars land might be way too tall for those kinds of precise needs to make any kind of difference.
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